クロルフェネシン
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- chlorphenesin carbamate
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/05/07 16:23:06」(JST)
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Chlorphenesin
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| Systematic (IUPAC) name |
| (3-(4-chlorophenoxy)-2-hydroxypropyl)carbamate |
| Clinical data |
| AHFS/Drugs.com |
Micromedex Detailed Consumer Information |
| Pregnancy cat. |
? |
| Legal status |
? |
| Pharmacokinetic data |
| Excretion |
urine |
| Identifiers |
| CAS number |
886-74-8 |
| ATC code |
D01AE07 |
| PubChem |
CID 2724 |
| ChemSpider |
2623 |
| UNII |
I670DAL4SZ Y |
| KEGG |
D00770 |
| ChEMBL |
CHEMBL607710 Y |
| Chemical data |
| Formula |
C10H12ClNO4 |
| Mol. mass |
245.660 g/mol |
| SMILES |
eMolecules & PubChem |
| Physical data |
| Melt. point |
86–92 °C (187–198 °F) |
Chlorphenesin (Maolate, Musil) is a centrally acting muscle relaxant used to treat muscle pain and spasms.[1][2]
It also has antifungal and some antibacterial properties and is thus classified as an antifungal for topical use by the WHO.[3]
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Contents
- 1 Safety
- 2 Physical Properties
- 3 Chemistry
- 4 References
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Safety
The adverse effects from this preservative on skin is allergic contact sensitivity.[4][5]
Physical Properties
Melting Point
86–92 deg. Celsius[6]
Chemistry
Chlorphenesin, 3-(4-chlorophenoxy)-1,2-propanediol, is synthesized in the same manner as methocarbamol from 3-(4-chlorophenoxy)-1,2-propanediol.[7][8][9]
References
- ^ Okuyama S, Aihara H (1987). "Antinociceptive effect of chlorphenesin carbamate in adjuvant arthritic rats". Research communications in chemical pathology and pharmacology 55 (2): 147–60. PMID 3823606.
- ^ Kurachi M, Aihara H (1984). "Effect of a muscle relaxant, chlorphenesin carbamate, on the spinal neurons of rats". Japanese journal of pharmacology 36 (1): 7–13. doi:10.1254/jjp.36.7. PMID 6503049.
- ^ ATC code D01AE07
- ^ Brown R (1981). "Chlorphenesin sensitivity". Contact Dermatitis 7 (3): 162. doi:10.1111/j.1600-0536.1981.tb04601.x. PMID 6456118.
- ^ Burns DA (1986). "Allergic contact sensitivity to chlorphenesin". Contact Dermatitis 14 (33): 246. doi:10.1111/j.1600-0536.1986.tb01234.x. PMID 2941223.
- ^ Salim E.F., Booth R.E. (1967). "Qualitative and quantitative tests for chlorphenesin carbamate". Journal of Pharmaceutical Sciences 56 (5): 623–4. doi:10.1002/jps.2600560516. PMID 6032776. http://www3.interscience.wiley.com/journal/113292953/abstract. Retrieved 2009-06-23.
- ^ J.R. Collins, M. Richard, U.S. Patent 3,161,567 (1964)
- ^ H.E. Perker, U.S. Patent 3,214,336 (1965)
- ^ J. Forrest, W. Bradley, GB 628497 (1948)
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Antifungals (D01 and J02)
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Wall/
membrane |
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Ergosterol
inhibitors
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Azoles
(lanosterol 14
alpha-demethylase inhibitors) |
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Imidazoles
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- topical: Bifonazole
- Butoconazole
- Clomidazole
- Clotrimazole#, Croconazole
- Econazole
- Fenticonazole
- Ketoconazole
- Isoconazole
- Miconazole#, Neticonazole
- Omoconazole
- Oxiconazole
- Sertaconazole
- Sulconazole
- Tioconazole
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Triazoles
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- topical: (Fluconazole#, Fosfluconazole
- Terconazole)
- systemic: (Fluconazole
- Hexaconazole
- Isavuconazole†, Itraconazole
- Posaconazole
- Voriconazole)
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Thiazoles
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topical: (Abafungin)
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Polyene antimycotics
(ergosterol binding)
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- topical: (Hamycin
- Natamycin
- Nystatin#)
systemic: (Amphotericin B#, Hamycin)
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Allylamines
(squalene monooxygenase
inhibitors) |
- topical: (Amorolfine
- Butenafine
- Naftifine
- Terbinafine)
systemic: (Terbinafine)
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β-glucan synthase
inhibitors
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- echinocandins (Anidulafungin
- Caspofungin
- Micafungin)
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| Intracellular |
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Pyrimidine analogues/
Thymidylate synthase inhibitors
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Mitotic inhibitors
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| Others |
- Bromochlorosalicylanilide
- Methylrosaniline
- Tribromometacresol
- Undecylenic acid
- Polynoxylin
- Chlorophetanol
- Chlorphenesin
- Ticlatone
- Sulbentine
- Ethyl hydroxybenzoate
- Haloprogin
- Salicylic acid
- Selenium sulfide#
- Ciclopirox
- Amorolfine
- Dimazole
- Tolnaftate
- Tolciclate
- Sodium thiosulfate#
- Whitfield's ointment#
- Potassium iodide#
- Taurolidine
- Tea tree oil
- citronella oil
- lemon grass
- orange oil
- patchouli
- lemon myrtle
- PCP: Pentamidine
- Dapsone
- Atovaquone
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Skeletal muscle relaxants (M03)
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Peripherally acting
(primarily antinicotinic,
NMJ block) |
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Non-depolarizing
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Curare alkaloids
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- Alcuronium
- Dimethyltubocurarine
- Tubocurarine
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4° ammonium agents
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- ultra-short duration: Gantacurium
- short duration: Mivacurium
- Chandonium
- intermediate duration: Atracurium
- Cisatracurium
- Fazadinium
- Rocuronium
- Vecuronium
- long duration: Doxacurium
- Dimethyltubocurarine
- Pancuronium
- Pipecuronium
- Laudexium
- Gallamine
- unsorted: Hexafluronium (Hexafluorenium)
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Depolarizing
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- Choline derivatives: Suxamethonium (Succinylcholine)
- Polyalkylene derivatives: Hexamethonium
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ACh release inhibitors
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| Centrally acting |
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Carbamic acid esters
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- Carisoprodol
- Cyclarbamate
- Difebarbamate
- Febarbamate
- Meprobamate
- Methocarbamol
- Phenprobamate
- Styramate
- Tybamate
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Benzodiazepines
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- Bentazepam
- Diazepam
- Lorazepam
- Nitrazepam
- Tetrazepam
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Anticholinergics (Antimuscarinics)
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- Cyclobenzaprine
- Orphenadrine
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Other
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- Baclofen
- Chlormezanone
- Chlorphenesin
- Chlorzoxazone
- Donepezil
- Eperisone
- Flopropione
- Mephenesin
- Mephenoxalone
- Metaxalone
- Phenyramidol
- Pridinol
- Promoxolane
- Quinine
- Thiocolchicoside
- Tizanidine
- Tolperisone
- Trazodone
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| Directly acting |
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anat (h/n, u, t/d, a/p, l)/phys/devp/hist
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noco(m, s, c)/cong(d)/tumr, sysi/epon, injr
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English Journal
- Contact allergy to chlorphenesin.
- Dyring-Andersen B1, Elberling J, Duus Johansen J, Zachariae C.
- Journal of the European Academy of Dermatology and Venereology : JEADV.J Eur Acad Dermatol Venereol.2015 May;29(5):1019. doi: 10.1111/jdv.12437. Epub 2014 Mar 14.
- PMID 24628968
- Occurrence of preservatives and antimicrobials in Japanese rivers.
- Kimura K1, Kameda Y2, Yamamoto H3, Nakada N4, Tamura I5, Miyazaki M6, Masunaga S7.
- Chemosphere.Chemosphere.2014 Jul;107:393-9. doi: 10.1016/j.chemosphere.2014.01.008. Epub 2014 Feb 18.
- We established a method for the simultaneous analysis of seven preservatives and five antimicrobials in water. These chemicals are widely used in cosmetics, and their presence in river water is of concern. We used the method to test 13 sites in Japanese rivers and streams contaminated by domestic wa
- PMID 24556546
- Safety Assessment of Chlorphenesin as Used in Cosmetics.
- Johnson W Jr1, Bergfeld WF2, Belsito DV2, Hill RA2, Klaassen CD2, Liebler DC2, Marks JG Jr2, Shank RC2, Slaga TJ2, Snyder PW2, Andersen FA3.
- International journal of toxicology.Int J Toxicol.2014 May 26;33(2 suppl):5S-15S. [Epub ahead of print]
- Chlorphenesin functions as a biocide in cosmetics and is used at concentrations up to 0.32% in rinse-off products and up to 0.3% in leave-on products. The Cosmetic Ingredient Review Expert Panel (Panel) noted that chlorphenesin was well absorbed when applied to the skin of rats; however, any safety
- PMID 24861369
Japanese Journal
- 高速液体クロマトグラフィーによる化粧品中の防腐剤クロルフェネシンの定量
- Kinetics and Mechanism of Degradation of Chlorphenesin Carbamate in Strongly Acidic Aqueous Solutions
- 原 松次,林 英文,吉田 継親
- Chemical & pharmaceutical bulletin 34(8), 3481-3484, 1986-08-25
- … The kinetics and mechanism of the degradation of chlorphenesin carbamate (α-CPC) in various strongly acidic aqueous solutions were studied at 40 to 60℃.The degradation of α-CPC obeyed pseudo first-order kinetics. … and -21.3 cal・deg^<-1>・mol^<-1>, respectively.Chlorphenesin was detected as the acidic degradation product of α-CPC. …
- NAID 110003626567
- Studies on the Kinetics and Mechanism of Drug Degradation. I. : Kinetics and Mechanism of Degradation of Chlorphenesin Carbamate in Strongly Alkaline Aqueous Solutions
- 原 松次,林 英文,吉田 継親,村山 普
- Chemical & pharmaceutical bulletin 34(4), 1764-1769, 1986-04-25
- … The kinetics and mechanism of the degradation of chlorphenesin carbamate (α-CPC) in strongly alkaline aqueous solutions were studied at 0 to 20℃. … Chlorphenesin-2-carbamate (β-CPC) and chlorphenesin (CP) were detected as alkaline degradation products of α-CPC.The mechanism proposed for the degradation of α-CPC involves migration of the carbamoyl group to the adjacent OH group and removal of the carbamoyl group in the presence of hydroxide ions. …
- NAID 110003626300
Related Links
- Chlorphenesin uses and safety reviewed by Truth In Aging ... * An organic compound. Functions: Primarily used as a pharmaceutical muscle relaxant, which works by blocking nerve impulses that are sent to the brain.
- 3 Percutaneous Absorption 14The percutaneous absorption of C-chlorphenesin was evaluated using 16 male rats of the Sprague-Dawley CD strain (~ 6 weeks old).15 14C-chlorphenesin (in 0.05% w/w cold cream; mean dose = 1.14 ...
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